Margaric acid, or heptadecanoic acid, is a saturated fatty acid. Its molecular formula is . Classified as an odd-chain fatty acid, it occurs as a trace component of the fat and milkfat of . Carboxylate salt and of margaric acid are called heptadecanoates.
Its name is derived from the Ancient Greek μάργαρος ( márgar(on)), meaning "pearl(y)", due to its appearance. The name is, in turn, the root of "margarine".[" Margarine", Etymonline; the online etymology dictionary; accessed 2025.09.15.]
Semiochemistry
For many species, margaric acid plays a role as a
semiochemical. Specifically, it possesses
Pheromone and
Allomone properties. Margaric acid has been identified in the subcaudal gland secretions of the
European badger (
Meles meles)
and in the occipital gland secretions of male
(
Camelus bactrianus) where it is one of the many pheromonic chemicals responsible for aiding in the finding and selection of mates.
Margaric acid is an attractant of the khapra beetle ( Trogoderma granarium) and the Aedes aegypti ( Aedes aegypti) but is a repellent of the Culex pipiens ( Culex pipiens).
Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko ( Eublepharis macularius) and the Adder ( Vipera berus), where it is used for the identification of sexual partners.
Unsaturated forms
Unsaturated derivatives of margaric acid are found in nature, although rarely. Unsaturation occurs at position 9 or both at 9 and 12 positions of the fatty chain giving heptadecenoic (C17:1) and heptadecadienoic (C17:2) acids, respectively. C17:1 cis-9 (ω-8) is found at trace amounts in
ruminant fats
and some varieties of
.
Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of portia tree (
Thespesia populnea).
Rarity in vegetable and animal fats
Margaric acid is rare in animals and vegetables.
In the 19th and early 20th centuries, however, the acid was often identified as a significant component of natural fats. Most likely, these were cases of misidentifying a
eutectic mixture of
palmitic and
stearic acids.
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See also
-
List of saturated fatty acids
-
List of carboxylic acids
-
Pentadecylic acid
External links